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In its contemporary iteration, preppy style witnesses time-honoured essentials like the blazer in fresh silhouettes, and conservative pieces like the loafer remixed with a platform heel for the modern era. Schoolgirl staples like the tunic are infused with a sense of rebelliousness and mixed with ’90s grunge for a an avatar cooler than any of its predecessors, and the substitute teacher sweater vest finds its place among the who’s who of fashion, with a playful update. Which would explain the popularity of fashion hashtags like “old money” and “academia” on TikTok and Instagram.
Princess Diana in a now-iconic sheep sweater by British label Warm & Wonderful
Getty Images/Tim Graham
Alicia Silverstone and Stacey Dash as Cher Horowitz and Dionne Davenport in Clueless
It’s also impossible to discuss preppy style without making a mention of two of its most ardent advocates—perpetual style icon Princess Diana, and legendary fictional It-girl, Clueless’s Cher Horowitz. While much has been written about why Princess Di has captured the imagination of the youth, it comes down to the fact that her ability to mix buttoned-up royal style with whimsy created an aesthetic that was made to last (and it has). Cher, on the other hand, pioneered the knee socks-and-skirt look, bringing a fresh and collegiate take on the three piece suit with her tartan skirts, vests and blazers.
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When trying to decode its appeal, what jumps to the fore is the timelessness that preppy-chic projects, and the sense of polish and put-togetherness that it imbues on its wearer. You don’t have to look far to see the preppy influence among fashion darlings, with model Gigi Hadid stepping out in many a collegiate-inspired look, from academic two-piece suits to the classic sweater-and-oxford combination. Closer to home, Khushi Kapoor’s Instagram provides much inspiration for the trend, with Kapoor favouring the pleated skirt in its 2020s avatar. If you’re looking for a way to channel the country club aesthetic, we suggest you equip yourself with cool-girl takes on school uniform staples like the blazer and an updated pair of mary janes, and investing in sweaters that can be thrown casually over your shoulders a la an early-’90s Gwyneth Paltrow
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What is the pantashoe and why does it have Kim Kardashian’s vote?
